100159-47-5

Basic information

• Product Name: 1H-Pyrazole, 1-(phenylmethoxy)-
• CAS NO: 100159-47-5
• Molecular Formula: C10H10N2O
• Molecular Weight: 174.202
• Mol File: 100159-47-5.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole, 1-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole, 1-(phenylmethoxy)-(100159-47-5)
• EPA Substance Registry System: 1H-Pyrazole, 1-(phenylmethoxy)-(100159-47-5)

Safety Data

• Hazardous Substances Data: 100159-47-5(Hazardous Substances Data)

Usage

Structure

Pyrazole ring with a phenylmethoxy substituent

Usage

Building block in the synthesis of various organic compounds in pharmaceutical and industrial sectors

Potential

Promising new class of bifunctional inhibitor for the treatment of various diseases, including cancer and infectious diseases

Value

Unique structure and properties make it a valuable tool for the development of novel drugs and materials

Research needs

Further research is needed to fully understand its potential applications and impacts on health and the environment.

Upstream product

• 100-39-0 benzyl bromide 
• 81945-73-5 1H-pyrazol-1-ol 

Downstream Products

• 166820-31-1 1-benzyloxypyrazol-5-carbaldehyde 
• 217313-04-7 1-Benzyloxy-5-thiophen-2-yl-1H-pyrazole 
• 217313-01-4 1-Benzyloxy-5-(2-methoxy-phenyl)-1H-pyrazole 
• 217312-98-6 1-(benzyloxy)-5-(2-fluorophenyl)pyrazole 
• 217313-00-3 2-(2-Benzyloxy-2H-pyrazol-3-yl)-phenylamine 
• 217313-03-6 2-(2-Benzyloxy-2H-pyrazol-3-yl)-benzaldehyde 
• 912574-86-8 1-benzyloxy-5-tributylstannanyl-1H-pyrazole 
• 166820-35-5 1-benzyloxy-5-iodopyrazole 
• 166820-34-4 1-(Benzyloxy)-5-bromopyrazole 
• 81945-73-5 1H-pyrazol-1-ol 

Relevant articles and documents

1H-QUINAZ0LINE-2,4-DIONES AND THEIR USE AS AMPA-RECEPTOR LIGANDS

The present invention relates to l H-Quinazoline-2,4-diones of formula (I) wherein R1 and R2 are as defined in the specification, their preparation, their use as AMPA-receptor ligands, in particular for the treatment of epilepsy or schizophrenia, and pharmaceutical compositions containing them. Further, intermediates for the manufacture of compounds of formula (I) and combinations comprising compounds of formula (I) are disclosed.

Regioselective introduction of electrophiles in the 4-position of 1- hydroxypyrazole via bromine-lithium exchange

Two protocols for introduction of electrophiles at the 4-position of 1- hydroxypyrazoles have been developed. The first is deprotonation of 4-bromo- 1-[(tert-butyldiphenylsilyl)oxy]pyrazole (6) with LDA to produce the 5-lithio derivative in which the silyl group migrates spontaneously from oxygen to C-5 affording 4-bromo-5-(tert-butyldiphenylsilyl)-1-lithoxypyrazole (8). Subsequent treatment with t-BuLi causes bromine-lithium exchange to give 5- tert-butyldiphenylsilyl-4-lithio-1-lithoxypyrazole which is trapped with electrophiles affording 4-substituted 5-(tert-butyldiphenylsilyl)-1- hydroxypyrazoles 9a-e in a one-pot sequence. The second is treatment of 4- bromo-1-hydroxypyrazole (5) with excess LDA and trimethylsilyl chloride to produce 3,5-bis(trimethylsilyl)-4-bromo-1-hydroxypyrazole (12), which upon sequential metalation with n-BuLi and reaction with electrophiles affords 4- substituted 3,5-bis(trimethylsilyl)-1-hydroxypyrazoles 13a-e. The tert- butyldiphenylsilyl group of 9a and the trimethylsilyl groups of 12 can be removed selectively by treatment with tetrabutylammonium fluoride in THF in the presence of trifluoroacetic acid.

Synthesis of 5-Substituted 1-Hydroxypyrazoles through Directed Lithiation of 1-(Benzyloxy)pyrazole

1-Hydroxypyrazoles have been converted to 1-(benzyloxy), , , and (silyloxy)pyrazoles. 1-(Benzyloxy)pyrazole was lithiated selectively in the 5-position.Subsequent reaction with electrophiles gives rise to 1-(benzyloxy)pyrazole with carbon, halogen, silicon, sulfur, or tin substituents at the 5-position. 1-(Benzyloxy)pyrazoles could be debenzylated by hydrogen bromide or hydrogenolysis producing 5-substituted 1-hydroxypyrazoles in high overall yield.